1. Why was there so much rancor between the United States and Cuba?

After pro-American dictator Fulgencio Batista was overthrown by Fidel Castro and his guerrilla force in a much-mythologized communist revolution, Cuba’s once-close relationship with the United States began to deteriorate. Fidel promised to not let America derail Cuba’s new independence. “The revolution begins now,” he proclaimed on January 1, 1959 — the day Batista’s regime fell. “This time, luckily for Cuba, the revolution will truly come into being. It will not be like 1895, when the North Americans came and took over,” he added, referring to the fact that after Cuba received its independence from Spain, the U.S. reserved the right to supervise its finances and foreign relations. That victory speech voiced the long-held anger at the United States for subjecting Cuba to its economically-based imperialist agenda. And the rift between the U.S. and Cuba that began that day, with the deposition of Batista, grew wider when Castro nationalized foreign property and companies and signed a trade agreement with the Soviet Union. Those actions prompted the Eisenhower administration to sever diplomatic ties with Cuba on January 3, 1961 and put in place an embargo. The failed Bay of Pigs invasion in 1961 and the Cuban Missile Crisis in 1962 only brought more animosity to the two countries’ ideological differences.

Even though the Cold War has been over for two decades and the Cuban economy is one of lines and shortages, the relationship between Cuba and the United States is still frosty; the ever-more controversial trade embargo remains. But on Wednesday, the Obama administration announced plans for normalizing relations, ending the last vestige of Cold War diplomacy and serving as the most significant change to the United States’ Cuban policy in 50 years — a stalemate that has outlasted 10 U.S. presidents. Three generations past the revolution, Cuban glasnost has begun.

President Barack Obama announced that “today, the United States of America is changing its relationship with the people of Cuba,” in a statement made at noon from the Cabinet Room at the White House. “Today, America chooses to cut loose the shackles of the past so as to reach for a better future — for the Cuban people, for the American people, for our entire hemisphere, and for the world,” he concluded, noting that the United States’ rigid policy was “rooted in events that took place before most of us were born.” Resuming diplomatic relations with Cuba will end what the president termed an “outdated approach” and a failed approach that neither helped “our interests” as a country nor brought the Castro regime any closer to democracy or restoring basic human rights.

“Proudly, the United States has supported democracy and human rights in Cuba through these five decades. We have done so primarily through policies that aimed to isolate the island, preventing the most basic travel and commerce that Americans can enjoy anyplace else,” Obama said. “And though this policy has been rooted in the best of intentions, no other nation joins us in imposing these sanctions, and it has had little effect beyond providing the Cuban government with a rationale for restrictions on its people. Today, Cuba is still governed by the Castros and the Communist Party that came to power half a century ago.”

2. Did Obama push for normalizing relations with Cuba as a presidential candidate?

As a candidate in 2008, speaking before an audience of influential Cuban-Americans in Miami, Obama criticized the United States’ policy of isolating Cuba. “After eight years of the disastrous policies of George Bush, it is time to pursue direct diplomacy, with friend and foe alike, without preconditions,” he pledged. He acknowledged that previous U.S. presidents had also made promises to the Cuban diaspora that failed to materialize. But he claimed to offer a straightforward “strategy for change.” Obama explained that his policy would be “guided by one word: Libertad. And the road to freedom for all Cubans must begin with justice for Cuba’s political prisoners, the rights of free speech, a free press and freedom of assembly; and it must lead to elections that are free and fair.” While he said the embargo would be kept in place, he promised to lift the travel ban for family members and allow unlimited remittances to the island. Obama said his message to Fidel and Raul Castro was, “if you take significant steps toward democracy, beginning with the freeing of all political prisoners, we will take steps to begin normalizing relations.” As Roger Cohen wrote for The New York Times just after the 2008 election, even Cubans believed Obama could change the status quo. “[O]n Havana’s streets the name Obama is often uttered as if it were a shibboleth. Many people want to believe he offers a way out of the Cuban web that Fidel’s infinite adroitness and intermittent ruthlessness have woven over a half-century.”

It has been many years since Obama made that promise. And it has been argued that the steps taken by his administration — like lifting the travel ban for family members, allowing unlimited remittances from Cuban-Americans, and broadening purposeful travel to Cuba for U.S. citizens — have produced real and measurable changes. But critics argue that those small steps have not changed the fact that the Cuban dictatorship “continues to violate human rights and shows no intention to make amends,” as Cuban-American journalist Carlos Alberto Montaner noted in an October 2014 opinion piece for the Times. “The small economic changes it has made are directed at strengthening the regime. Why reward that behavior?”

3. Who is Alan Gross?

But policy experts and journalists see changes in Cuba that Montaner’s analysis swept over. The release of Alan Gross — an elderly government subcontractor, who was detained in December 2009 for delivering communications equipment to religious groups and sentenced to 15 years in prison for plotting to “destroy the revolution” — does mark an important moment in Cuban-American relations. The arrest, which came approximately nine months after Obama loosened travel restrictions for Cuban-Americans, did set back any chance of reconciliation; Cuban officials argued the country was merely protecting its sovereignty, while Americans claimed it was a human rights violation. His release is a small piece of evidence that the country stands at the fulcrum of the “generational shift” that Cohen described in his piece, “The End of the End of the Revolution,” although more compelling examples exist. More specifically, it was Castro’s decision to release Gross that put the two countries on a path to normalcy; the release of political prisoners was one of Obama’s conditions for a normalized relationship.

Three Cuban spies (members of the so-called Cuban Five) who had been imprisoned in America since 2001 were returned to Cuba, but American officials told the Times the release of Gross was not part of that prisoner exchange.

4. What does normalizing relations actually mean?

After 18 months of negotiations brokered by Pope Francis, Obama and Cuban President Raul Castro, who is much more of a pragmatist than his older brother, set the terms of the return to normalcy. During a 45-minute telephone call on Tuesday — the first direct communication between the heads of the American and Cuban governments in 50 years — they agreed to exchange ambassadors, reopen embassies, and hold bilateral discussions. Obama does have some room to ease the trade restrictions, and he indicated he would do as much as in his power, but to repeal all sanctions requires an act of Congress. Wednesday, both men simultaneously announced the thaw. Castro acknowledged a need for change by noting “we must learn the art of coexisting with our differences in a civilized manner,” while Obama kept his comments more focused on the concept of liberty, quoting Cuban revolutionary philosopher José Martí.

5. Why is Obama drawing criticism for normalizing relations?

The criticism has already begun; a growing number of U.S. lawmakers believe that little can be gained by keeping Cuba diplomatically isolated. But a pushback can be expected. As Wayne Smith — who ran the U.S. interest section in Havana, which represented U.S. interests in Cuba in lieu of an embassy — observed in an interview with the Times: “Cuba seems to have the same effect on American administrations that the full moon used to have on werewolves.” Obama’s decision to begin diplomatic relations with the still-communist state could be a supermoon for Republican lawmakers. “Relations with the Castro regime should not be revisited, let alone normalized, until the Cuban people enjoy freedom – and not one second sooner,” House Speaker John A. Boehner, an Ohio Republican, said in a statement. Criticism even spilled across the partisan divided. “This is a reward that a totalitarian regime does not deserve, and this announcement only perpetuates the Castro regime’s decades of repression,” outgoing Senate Foreign Relations Committee Chairman Robert Menendez, a New Jersey Democrat, said in a blunt statement.

Republican Marco Rubio, a Cuban-American senator from Florida, was even more critical. He called Obama’s decision “another concession to tyranny” by his administration. “The Cuban people — like all those oppressed around the world — they look to America to stand up for these rights, to live up to our commitment to the God-given right of every person, to life, liberty and pursuit of happiness.” Rubio said it is “unacceptable that the only people in this hemisphere that have not known democracy … are the people of Cuba.” The senator said he will only support normalizing relations with Cuba after democratic elections occur, and he pledged to block the president’s diplomatic efforts as incoming Chairman of the Senate Foreign Relations Committee. Part of his opposition is surely political; Rubio stands to benefit from taking a sharp stand on foreign affairs if he intends to run for the GOP presidential nomination. However, his opposition also speaks to the larger mood of the Cuban-American exile population in Florida, who see Fidel Castro as the dictator who kicked them out of their homeland.

But is important to remember not all share that rancor, and that reality means that Obama’s decision was not as unilateral as his critics believe. Even the 2008 election and 2012 reelection of Obama is a testament to that fact. As a candidate in 2008, he took a new view on Cuba, rejecting the Bush administration’s “tough talk that never yields results,” and called for a new strategy that set the two countries on the path to diplomatic recognition. The Cuban-American vote, though small, has long been seen as an important demographic in presidential elections. After all, Florida is a key swing state. For decades, Cuban-Americans were strongly Republican, with their political allegiance shaped by Cold War rhetoric. The Republicans strongly anti-communist stance fit well with the anti-Castro Cuban exiles, for whom a hard line toward Fidel’s Cuba was a winning political platform. However, a 2013 Pew survey found that the Republican advantage among Cuban-American voters had shrunk by three percentage points, from 47% to 44%, while the 2012 Florida exit poll showed that Obama won the Cuban-American vote by two percentage points. And while poll data is notably a small snapshot of a larger and more complex reality, those figures do show that being a Democrat is no longer equated by Cuban-Americans as being a communist.

Sure, some backsliding will follow. As Obama noted, “we are separated by just over 90 miles. But year after year, an ideological and economic barrier hardened between our two countries.”